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WO1985004577A1 - Compositions stimulant la croissance des cheveux - Google Patents

Compositions stimulant la croissance des cheveux Download PDF

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Publication number
WO1985004577A1
WO1985004577A1 PCT/US1985/000556 US8500556W WO8504577A1 WO 1985004577 A1 WO1985004577 A1 WO 1985004577A1 US 8500556 W US8500556 W US 8500556W WO 8504577 A1 WO8504577 A1 WO 8504577A1
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WO
WIPO (PCT)
Prior art keywords
methyl
dihydro
pyrimidine
butyl
pyridyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1985/000556
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English (en)
Inventor
Gail Sansone Bazzano
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
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Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of WO1985004577A1 publication Critical patent/WO1985004577A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth

Definitions

  • the present invention relates to topical application of Compounds A, B, C, D, series and methyl 5- ⁇ 3, 6-dihydro-1(2H)-pyridyl>-2-oxo-2H- ⁇ 1, 2, 4> oxadiazolo 2,3,- ⁇ > pyrimidine-7-carbamate and their active analogs and derivatives for improving the rate of hair growth on mammalian skins and for the treatment of alopecia, as well as the use of the forementioned compounds and their analogs with retinoids.
  • a normal characteristic of hair growth in mammals, including human, is that in most cases the rate of hair growth and the length of its growth cycle are reduced with age. These phenomena are common to all mammals with rare exceptions and they must be differentiated from true male pattern alopecia.
  • United States Patent No. 4,139,619 issued to Charles A. Chidsey on February 13, 1979 discloses a process for stimulating the growth of mammalian hair by topical application of certain preparations containing, as the active ingredient, 6-amino-4 (substituted amino)-1,2-dehydro-1-hydroxy-2-iminopyrimidine.
  • This patent further states that the active compounds and the methods of their preparations are disclosed in United States Patent No. 3,461,461, which was issued on August 12, 1969.
  • Most examples in the patent to Chidsey describe various preparations such as topical cream, topical ointment, solution, aerosol and dusting powder, and state that these preparations can be applied to the bald human scalp to stimulate the rate of growth of terminal hair.
  • compositions for topical applications to mammalian skin, in combination with retinoids, in order to stimulate or improve the rate of hair growth thereon and to prolong the anagen phase of the hair cycle.
  • the subject compounds when applied to a mammalian skin, in an effective amount, stimulate or improve the rate of hair growth and prolong the anagen phase of the hair cycle. Moreover, these compounds have also been found to be effective in treatment of alopecia. Typically, these compounds constitute the active ingredients of different types of preparations such as lotions, solutions, ointments, creams, sprays and the like.
  • the compounds of the present invention which form the active ingredients in the hair treatment preparations include Compounds A, B, C, D, series and methyl 5- ⁇ 3, 6-dihydro-1(2H)-pyridyl-2-oxo-2H— ⁇ 1 , 2, 4>oxadiaolo ⁇ 2, 3- ⁇ >pyrimidine-7-carbamate or their active derivatives or analogs. Furthermore, combinations of these compounds with retinoids as described in PCT U.S./00338 and PCT U.S. 82/01593 exhibit synergism in that they improve or stimulate the rate of hair growth to a greater extent than the individual active ingredients of the combination alone.
  • Suitable retinoid active ingredients for use in this invention include derivatives of retinoic acid which have been described in PCT applications: U.S. 81/00338 and U.S. 82/01593.
  • Preparations such as lotions, creams, conditioners, and the like, including the aforementioned compounds as the active ingredients, can be applied topically to the skin for stimulating or improving the rate of hair growth. It has surprisingly been discovered that the compounds of the present invention, in comparison with minoxidil, when applied topically to the skin have excellent penetration and a long lasting effect, in producing hair growth in an animal model for androgenetic alopecia. Furthermore, retinoids in combination with the subject compounds of this application exhibit synergism in the animal model studied.
  • retinoid denotes retinol, retinal, retinyl esters as well as retinoic acid and its esters, amides, derivatives, analogs and metabolites.
  • the terminal groups may be oxidized, reduced, esterifled, etc.
  • the alkali metal (sodium, potassium, etc.) and alkaline earth metals (magnesium, zinc, calcium, etc.) salts of these compounds are also included herein.
  • the pharmaceutical, cosmetic or veterinary preparations of the present invention can be prepared by conventional techniques for the preparation of lotions, creams, conditioners or shampoos for the scalp or veterinary preparations for pelis. Included also are preparations which can be administered orally and compounds which can be added to animal foods.
  • the various preparations can contain any conventional pharmaceutically acceptable or cosmetically acceptable inert or pharmacodynamically active additives or carriers.
  • the lotions may be prepared using various forms of alcohols or other solubilizers such as glycols, or esters.
  • the conditioners may contain the normally acceptable commercially produced compounds such as cetyl alcohol, ceteareth-5, -20 hydrantoins, hydrolyzed animal protein, blycol stearate, amodimethicone, paraffin, mineral oil, etc.
  • the topical compounds may also contain various oils including essential fatty acids and phospholipids and other polyunsaturated fatty acids and their derivatives and.
  • the topically applied lotions, creams, and conditioners, etc. will vary according to the standard art with regard to the amounts of other hydrophilic and hydrophobic containing ingredients, including emulsifiers, so that either an oily, semi-oily or oil-free product may be obtained.
  • the shampoos may contain any of the conventionally used detergents or soaps and any other compounds used by those familiar with the art. Oil-based shampoos are included in these formulations.
  • the topical treatments may consist of lotions, creams, conditioners, shampoos, oil treatments, etc., with from 0.001 to 5% by weight of the active ingredients, Compounds A, B, C, D, series and all-trans retinoic acid or derivatives, or other retinoids, as the preferred dosages in these compositions.
  • R can be equal to : R can be equal to
  • R can be equal to a) methyl, b) ethyl, c) butyl, d) i-butyl, e) methoxy ethyl or f) allyl
  • R can be equal to a) methyl, b) ethyl, c) butyl, d) i-butyl, e) benzyl, or f) 2-methoxy ethyl
  • Components Weight % Active Ingredient Compound A methyl-5-[3,6-dihydro-1(2H)-pyridyl] 1.0 -2-oxo-2H-[1,2,4]-oxadiazolo[2,3-a] pyrimidine-7-carbamate
  • the water washable cream ointment thus prepared consists of 0.1% retinoic acid ingredient and 3% of Compound A (methyl-5-[3,6-dihydro-1(2H)-pyridyl]-2-oxo-2H-[1,2,4]-oxadiazolo[2,3-a] pyrimidine-7-carbamate).
  • Cream Conditioner for Topical Administration Weight %

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)

Abstract

Utilisation de pyrimidines substituées désignées comme séries de composés A, B, C, D et de 5-<3, 6-dihydro-1(2H)-pyridyl>-2-oxo-2H-<1, 2, 4>oxadiazolo<2, 3, -alpha>pyrimidine-7-carbamate de méthyle et de leurs dérivés et analogues actifs et de combinaisons de ces composés avec des rétinoïdes pour augmenter la vitesse de croissance des cheveux, et pour prolonger la phase anagène du cycle capillaire et traiter certains types d'alopécie.
PCT/US1985/000556 1984-04-06 1985-04-02 Compositions stimulant la croissance des cheveux Ceased WO1985004577A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US59725284A 1984-04-06 1984-04-06
US597,252 1984-04-06
US62475884A 1984-06-26 1984-06-26
US624,758 1984-06-26

Publications (1)

Publication Number Publication Date
WO1985004577A1 true WO1985004577A1 (fr) 1985-10-24

Family

ID=27082777

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1985/000556 Ceased WO1985004577A1 (fr) 1984-04-06 1985-04-02 Compositions stimulant la croissance des cheveux

Country Status (2)

Country Link
EP (1) EP0177581A4 (fr)
WO (1) WO1985004577A1 (fr)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0187854A4 (fr) * 1984-07-13 1987-01-22 Gail S Bazzano Oxydes de pyrimidine substitues utiles pour favoriser la croissance des cheveux.
WO1988001502A1 (fr) * 1986-09-05 1988-03-10 The Upjohn Company Composition de minoxydile non aqueuse de dissolution du sebum
WO1989000996A1 (fr) * 1987-07-31 1989-02-09 L'oreal Nouvelles oxadiazolo pyrimidinones, leur preparation et leur utilisation en cosmetique et dermopharmacie
US4832946A (en) * 1986-12-23 1989-05-23 Green Martin R Cosmetic composition
EP0319027A1 (fr) * 1987-12-04 1989-06-07 L'oreal Composition pour induire et stimuler la croissance des cheveux et/ou freiner leur chute, à base d'un tensio-actif non ionique et d'un dérivé de pyrimidine
WO1989006530A1 (fr) * 1988-01-21 1989-07-27 Leo Pharmaceutical Products Ltd. A/S (Løvens Kemis Nouvelle preparation topique servant au traitement de l'alopecie
US4871839A (en) * 1986-03-14 1989-10-03 Lever Brothers Company Skin treatment composition
US4975441A (en) * 1988-03-23 1990-12-04 Unilever Patent Holdings B.V. Lactams, their synthesis and use in cosmetic compositions
US5015470A (en) * 1986-12-23 1991-05-14 Gibson Walter T Cosmetic composition
US5026691A (en) * 1987-03-30 1991-06-25 The Upjohn Company Combination of minoxidil and an antiinflammatory agent for treating patterned alopecia
US5037643A (en) * 1988-03-23 1991-08-06 Unilever Patent Holdings, B.V. Cosmetic composition
EP0459890A1 (fr) * 1990-05-30 1991-12-04 L'oreal Composition destinée à être utilisée pour freiner la chute des cheveux et pour induire et stimuler leur croissance,contenant des dérivés d'alkyl-2 amino-4 (ou dialkyl-2,4) pyrimidine oxyde-3 et nouveaux composés dérivés d'alkyl-2 amino-4 pyrimidine oxyde-3
EP0403238A3 (fr) * 1989-06-14 1992-03-04 Unilever Plc Composition cosmétique
US5358714A (en) * 1988-03-23 1994-10-25 Unilever Patent Holdings B.V. Cosmetic composition
AT400516B (de) * 1987-08-12 1996-01-25 Oreal Mittel zur induktion und stimulation des haarwuchses und zur verringerung von haarausfall auf basis eines retinoids und eines pyrimidinderivates
US5772990A (en) * 1991-06-20 1998-06-30 L'oreal Composition for slowing down the loss of hair based on pyrimidine N-oxides triaminosubstituted or their sulfoconjugated
WO1999062484A1 (fr) * 1998-06-03 1999-12-09 Gpi Nil Holdings, Inc. Compositions pour la croissance des cheveux a base de petites molecules de carbamates ou d'urees et utilisation de ces compositions
US6331537B1 (en) 1998-06-03 2001-12-18 Gpi Nil Holdings, Inc. Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds
US7078424B2 (en) 1998-06-03 2006-07-18 Gpi Nil Holdings, Inc. N-linked sulfonamides of N-heterocyclic carboxylic acids or carboxylic acid isosteres

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4129662A (en) * 1975-11-03 1978-12-12 Johnson & Johnson Retinoic acid derivatives for the treatment of acne
US4190594A (en) * 1975-11-03 1980-02-26 Johnson & Johnson Retinoic acid derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1983002558A1 (fr) * 1981-11-09 1983-08-04 Gail Sansone Bazzano Utilisation de retinoides et minoxydile (2,4,-diamino-6-piperidino-pyrimidine-3-oxyde) pour ameliorer le taux de croissance des cheveux et traiter certains types d'alopecies chez l'homme

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4129662A (en) * 1975-11-03 1978-12-12 Johnson & Johnson Retinoic acid derivatives for the treatment of acne
US4190594A (en) * 1975-11-03 1980-02-26 Johnson & Johnson Retinoic acid derivatives

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
FDA Consumer, February, 1981, Vol. 15, No. 1, see pages 10 and 12 *
See also references of EP0177581A4 *

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0187854A4 (fr) * 1984-07-13 1987-01-22 Gail S Bazzano Oxydes de pyrimidine substitues utiles pour favoriser la croissance des cheveux.
US4871839A (en) * 1986-03-14 1989-10-03 Lever Brothers Company Skin treatment composition
WO1988001502A1 (fr) * 1986-09-05 1988-03-10 The Upjohn Company Composition de minoxydile non aqueuse de dissolution du sebum
US4832946A (en) * 1986-12-23 1989-05-23 Green Martin R Cosmetic composition
US5015470A (en) * 1986-12-23 1991-05-14 Gibson Walter T Cosmetic composition
US5026691A (en) * 1987-03-30 1991-06-25 The Upjohn Company Combination of minoxidil and an antiinflammatory agent for treating patterned alopecia
EP0303871A1 (fr) * 1987-07-31 1989-02-22 L'oreal Oxadiazolo pyrimidinones, leur préparation et leur utilisation en cosmétique et dermopharmacie
WO1989000996A1 (fr) * 1987-07-31 1989-02-09 L'oreal Nouvelles oxadiazolo pyrimidinones, leur preparation et leur utilisation en cosmetique et dermopharmacie
AT400516B (de) * 1987-08-12 1996-01-25 Oreal Mittel zur induktion und stimulation des haarwuchses und zur verringerung von haarausfall auf basis eines retinoids und eines pyrimidinderivates
EP0319027A1 (fr) * 1987-12-04 1989-06-07 L'oreal Composition pour induire et stimuler la croissance des cheveux et/ou freiner leur chute, à base d'un tensio-actif non ionique et d'un dérivé de pyrimidine
WO1989006530A1 (fr) * 1988-01-21 1989-07-27 Leo Pharmaceutical Products Ltd. A/S (Løvens Kemis Nouvelle preparation topique servant au traitement de l'alopecie
US4975441A (en) * 1988-03-23 1990-12-04 Unilever Patent Holdings B.V. Lactams, their synthesis and use in cosmetic compositions
US5358714A (en) * 1988-03-23 1994-10-25 Unilever Patent Holdings B.V. Cosmetic composition
US5037643A (en) * 1988-03-23 1991-08-06 Unilever Patent Holdings, B.V. Cosmetic composition
EP0403238A3 (fr) * 1989-06-14 1992-03-04 Unilever Plc Composition cosmétique
EP0459890A1 (fr) * 1990-05-30 1991-12-04 L'oreal Composition destinée à être utilisée pour freiner la chute des cheveux et pour induire et stimuler leur croissance,contenant des dérivés d'alkyl-2 amino-4 (ou dialkyl-2,4) pyrimidine oxyde-3 et nouveaux composés dérivés d'alkyl-2 amino-4 pyrimidine oxyde-3
US5438058A (en) * 1990-05-30 1995-08-01 L'oreal Composition intended to be used for retarding hair loss and for inducing and stimulating hair growth, containing 2-alkyl-4-aminopyrimidine (or 2,4-dialkylpyrimidine) 3-oxide derivatives and new compounds derived from 2-alkyl-4-aminopyrimidine 3-oxide
FR2662607A1 (fr) * 1990-05-30 1991-12-06 Oreal Composition destinee a etre utilisee pour freiner la chute des cheveux et pour induire et stimuler leur croissance, contenant des derives d'alkyl-2 amino-4 (ou dialkyl-2-4) pyrimidine oxyde-3 .
US5772990A (en) * 1991-06-20 1998-06-30 L'oreal Composition for slowing down the loss of hair based on pyrimidine N-oxides triaminosubstituted or their sulfoconjugated
WO1999062484A1 (fr) * 1998-06-03 1999-12-09 Gpi Nil Holdings, Inc. Compositions pour la croissance des cheveux a base de petites molecules de carbamates ou d'urees et utilisation de ces compositions
US6331537B1 (en) 1998-06-03 2001-12-18 Gpi Nil Holdings, Inc. Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds
AU764032B2 (en) * 1998-06-03 2003-08-07 Gpi Nil Holdings, Inc. Small molecule carbamate or urea hair growth compositions and uses
US7078424B2 (en) 1998-06-03 2006-07-18 Gpi Nil Holdings, Inc. N-linked sulfonamides of N-heterocyclic carboxylic acids or carboxylic acid isosteres
US7153883B2 (en) 1998-06-03 2006-12-26 Gpi Nil Holdings Inc. Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds

Also Published As

Publication number Publication date
EP0177581A1 (fr) 1986-04-16
EP0177581A4 (fr) 1987-08-10

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